Benjamin Brink/The OregonianJefferson Smith stands at the podium in the grass at Terry Schrunk Plaza across from Portland City Hall to answer questions about what he called, "The worst night of my life." His remarks and the questions centered on a 1993 misdemeanor assault charge involving a woman when he was in college.

For the better part of eight weeks, Portland mayoral candidate Jefferson Smith has had to answer questions about his judgment over repeated driver's license suspensions and now a 19-year-old incident in which he hit a woman in the face.

The question now: Is Smith's candidacy damaged beyond repair?

The answer: He's dug himself into a deep, dark hole that will be exceedingly difficult -- but not impossible -- to climb out of, according to political observers, campaign experts, former local elected officials and city voters.

"I think he's in a great deal of trouble," said political science professor Jim Moore, director of the Tom McCall Center for Policy Innovation at Pacific University. "When there's a pattern, people respond to that pattern."

In a statement Tuesday night, the Smith campaign wrote that five witnesses backed up Smith's memory of events early Oct. 17, 1993.

"Our campaign has been counted out before," campaign manager Henry Kraemer wrote. "We were projected to finish a distant third in the primary, and our volunteers and supporters pulled off an underdog surprise."

But some said major damage has been done. Coupled with his license suspensions, this marks the second time since August that Smith has been less than forthcoming about his record.

Observers said those decisions may damage Smith's credibility or, at best, make it difficult to distinguish between Smith and opponent Charlie Hales, who has had his own blunders.

"If that were really the only event, and he'd been straight with it, I'd say I think he can probably manage. But when you've got a series of things," said former Portland city Commissioner Margaret Strachan, who is visiting Portland and follows local races from her Montana home. "Do I think he can come back? I think that it's going to be really tough. But I wouldn't rule it out."

Political insiders and others with experience running campaigns, who requested anonymity because of Oregon's small political world, had varying degrees of doom and gloom for Smith. "Instead of two days of news, it's two weeks of news," said one. "It's a huge strategic mistake."

Said another: "Is this a crack big enough to be able to bring down the house? It's possible."

\At a Tuesday debate hosted by Oregon Public Broadcasting, Smith denied having met and propositioned the woman in 1993, as the woman said in Eugene police records. "I'd think I'd remember," Smith said.

Smith's campaign also released a copy of the handwritten letter he wrote to the woman last Wednesday. Smith said the letter did not violate terms of a 1994 diversion agreement, an assertion supported by attorneys not connected to him. "I felt sorry then; I feel sorry now," Smith wrote in the letter. "It was an accident."

But John Bassett, the woman's lawyer, retorted: "It was no accident. He hit her in the left forehead, splitting her eyebrow." He added: "All of those attempts to dance around what took place are in stark contrast with his admission 19 years ago," in which Smith told police he "tagged" her with his fist.

Len Bergstein, a Portland political consultant and lobbyist, said the latest revelations could have been "deadly" if they surfaced as voters started getting their ballots Oct. 19.

And comparisons to former U.S. Rep. David Wu, who in 2004 faced questions about an attempted sexual assault at Stanford University in the 1970s, go only so far, he said. Wu was running for his fourth term in Congress and had a track record with voters. Although Smith has served two terms in the Oregon House representing east Portland, he "is still an unknown quantity to much of the electorate," he said.